AFCDB: (3R,3'S,6'R)-b,e-Carotene-3,3'-diol (FDB112373)

Record Information

Version

1.0

Creation date

2020-04-20 20:03:03 UTC

Update date

2020-04-21 18:03:41 UTC

Primary ID

FDB112373

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(3R,3'S,6'R)-b,e-Carotene-3,3'-diol

Description

(3R,3'S,6'R)-b,e-Carotene-3,3'-diol, also known as 3'-epilutein or (3R,3's,6'r)-lutein, belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Thus, (3R,3's,6'r)-b,e-carotene-3,3'-diol is considered to be an isoprenoid. Based on a literature review very few articles have been published on (3R,3'S,6'R)-b,e-Carotene-3,3'-diol.

CAS Number

Not Available

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00073 g/L	ALOGPS
logP	8.29	ALOGPS
logP	8.55	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	18.22	ChemAxon
pKa (Strongest Basic)	-0.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	195.06 m³·mol⁻¹	ChemAxon
Polarizability	73.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C40H56O2

IUPAC name

(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4S)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol

InChI Identifier

InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-,37+/m1/s1

InChI Key

KBPHJBAIARWVSC-IRHPOQNPSA-N

Isomeric SMILES

C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C

Average Molecular Weight

568.886

Monoisotopic Molecular Weight

568.428031043

Classification

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

C40 isoprenoids (tetraterpenes) (LMPR01070030 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(3R,3'S,6'R)-b,e-Carotene-3,3'-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uk9-1000190000-79574985e26da720cbd6	Spectrum
Predicted GC-MS	(3R,3'S,6'R)-b,e-Carotene-3,3'-diol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-3100039000-baee6b30a2822c061477	Spectrum
Predicted GC-MS	(3R,3'S,6'R)-b,e-Carotene-3,3'-diol, "(3R,3'S,6'R)-b,e-Carotene-3,3'-diol,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3R,3'S,6'R)-b,e-Carotene-3,3'-diol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3R,3'S,6'R)-b,e-Carotene-3,3'-diol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3R,3'S,6'R)-b,e-Carotene-3,3'-diol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3R,3'S,6'R)-b,e-Carotene-3,3'-diol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3R,3'S,6'R)-b,e-Carotene-3,3'-diol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-0201190000-12a2e7baec2965c164cf	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0829330000-021e7fc06b639da39e2c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000b-3339330000-4e6e49a5efd708c6c971	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000090000-cbb0d37d0ab268305e5e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0000090000-d81cdc000e19ba6b5a35	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uxr-0343390000-ff8fd45055c84409ffdb	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0202090000-e7ff503087b047287234	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0405490000-4908259aa27c690d5b58	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0201-0519300000-3ec7b022b5aedb2ab3d0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0121930000-b93c4284d63c87f0039c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uel-0113920000-f619218ed5b32e075e70	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0wmi-0059500000-ba48ee62bc6ea7e22dbf	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

(3R,3'S,6'R)-b,e-Carotene-3,3'-diol (FDB112373)

Structure for FDB112373 ((3R,3'S,6'R)-b,e-Carotene-3,3'-diol)